benzyl ether of (E)-dehydromarchantin I

Base Information

• Chemical Name: benzyl ether of (E)-dehydromarchantin I
• CAS No.: 208399-59-1
• Molecular Formula: C₃₆H₃₀O₄
• Molecular Weight: 526.632
• Mol file: 208399-59-1.mol

Synonyms:benzyl ether of (E)-dehydromarchantin I

Chemical Property of benzyl ether of (E)-dehydromarchantin I

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl ether of (E)-dehydromarchantin I

There total 18 articles about benzyl ether of (E)-dehydromarchantin I which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

[4-(2-Benzyloxy-5-{2-[3-(2-formyl-4-methoxy-phenoxy)-phenyl]-ethyl}-phenoxy)-benzyl]-triphenyl-phosphonium; bromide → benzyl ether of (E)-dehydromarchantin I (208399-59-1)

Guidance literature:

With sodium methylate; In dichloromethane; 15 h, 20 deg C, 1 h, reflux;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<877::AID-EJOC877>3.0.CO;2-S

Reference yield:

methyl 3-nitro-4-chlorobenzoate (14719-83-6) → benzyl ether of (E)-dehydromarchantin I (208399-59-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) NaH / 1.) DMF, 20 deg C, 10 min; 2.) DMF, 20 deg C, 2 h

2: 85 percent / 5percent Pd/C, H₂ / ethyl acetate / 6 h / 3750.3 Torr

3: 84 percent / NaNO₂, 50percent H₃PO₂ / H₂O / 2 h, 0 deg C, 5 h, 20 deg C

4: 81 percent / AlCl₃ / benzene / 15 h / Heating

5: 81 percent / Na₂CO₃ / ethanol; H₂O / 5 h / 20 °C

6: NBS, AIBN / CCl₄ / 2 h / Heating

7: toluene / 15 h / 100 °C

8: 89 percent / K₂CO₃, 18-crown-6 / CH₂Cl₂ / 24 h / Heating

9: 94 percent / 5percent Pd/C, H₂, triethylamine / ethyl acetate / 12 h / 3750.3 Torr

10: 1.) LiAlH₄; 2.) satd. NH₄Cl / 1.) diethyl ether, 5 h, reflux

11: 88 percent / K₂CO₃ / dimethylformamide / 2 h / 120 °C

12: 33percent HBr / diethyl ether; acetic acid / 2 h / 20 °C

13: toluene / 15 h / 100 °C

14: 81 percent / NaOCH₃ / CH₂Cl₂ / 15 h, 20 deg C, 1 h, reflux

With palladium on activated charcoal; N-Bromosuccinimide; lithium aluminium tetrahydride; aluminium trichloride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); hydrogen bromide; hydrogen; sodium methylate; hypophosphorous acid; sodium hydride; sodium carbonate; potassium carbonate; ammonium chloride; triethylamine; sodium nitrite; In tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<877::AID-EJOC877>3.0.CO;2-S

Reference yield:

5-methyl-2-methoxyphenol (1195-09-1) → benzyl ether of (E)-dehydromarchantin I (208399-59-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) NaH / 1.) DMF, 20 deg C, 10 min; 2.) DMF, 20 deg C, 2 h

2: 85 percent / 5percent Pd/C, H₂ / ethyl acetate / 6 h / 3750.3 Torr

3: 84 percent / NaNO₂, 50percent H₃PO₂ / H₂O / 2 h, 0 deg C, 5 h, 20 deg C

4: 81 percent / AlCl₃ / benzene / 15 h / Heating

5: 81 percent / Na₂CO₃ / ethanol; H₂O / 5 h / 20 °C

6: NBS, AIBN / CCl₄ / 2 h / Heating

7: toluene / 15 h / 100 °C

8: 89 percent / K₂CO₃, 18-crown-6 / CH₂Cl₂ / 24 h / Heating

9: 94 percent / 5percent Pd/C, H₂, triethylamine / ethyl acetate / 12 h / 3750.3 Torr

10: 1.) LiAlH₄; 2.) satd. NH₄Cl / 1.) diethyl ether, 5 h, reflux

11: 88 percent / K₂CO₃ / dimethylformamide / 2 h / 120 °C

12: 33percent HBr / diethyl ether; acetic acid / 2 h / 20 °C

13: toluene / 15 h / 100 °C

14: 81 percent / NaOCH₃ / CH₂Cl₂ / 15 h, 20 deg C, 1 h, reflux

With palladium on activated charcoal; N-Bromosuccinimide; lithium aluminium tetrahydride; aluminium trichloride; 18-crown-6 ether; 2,2'-azobis(isobutyronitrile); hydrogen bromide; hydrogen; sodium methylate; hypophosphorous acid; sodium hydride; sodium carbonate; potassium carbonate; ammonium chloride; triethylamine; sodium nitrite; In tetrachloromethane; diethyl ether; ethanol; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1002/(SICI)1099-0690(199805)1998:5<877::AID-EJOC877>3.0.CO;2-S

upstream raw materials:

methyl 3-nitro-4-chlorobenzoate

5-methyl-2-methoxyphenol

meta-hydroxybenzaldehyde

2-Bromo-5-methoxybenzaldehyde ethylene glycol acetal

Refernces